Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides

A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-05, Vol.71 (11), p.4170-4177
Main Authors: Zhang, Xuejun, Zhang, Yanshi, Huang, Jian, Hsung, Richard P, Kurtz, Kimberly C. M, Oppenheimer, Jossian, Petersen, Matthew E, Sagamanova, Irina K, Shen, Lichun, Tracey, Michael R
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Bromides - chemistry
Catalysis
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Macrocyclic Compounds - chemical synthesis
Molecular Conformation
Organic chemistry
Preparations and properties
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Summary:A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060230h